NO309526B1 - Hetero-aromatiske ring-substituerte fenyloksazolidinon- antimikrobielle midler og anvendelse av disse for fremstilling av et medikament - Google Patents
Hetero-aromatiske ring-substituerte fenyloksazolidinon- antimikrobielle midler og anvendelse av disse for fremstilling av et medikament Download PDFInfo
- Publication number
- NO309526B1 NO309526B1 NO973550A NO973550A NO309526B1 NO 309526 B1 NO309526 B1 NO 309526B1 NO 973550 A NO973550 A NO 973550A NO 973550 A NO973550 A NO 973550A NO 309526 B1 NO309526 B1 NO 309526B1
- Authority
- NO
- Norway
- Prior art keywords
- mmol
- solution
- fluoro
- phenyl
- treated
- Prior art date
Links
- 125000001072 heteroaryl group Chemical group 0.000 title claims abstract description 9
- 239000003814 drug Substances 0.000 title claims description 5
- NCTCGHLIHJJIBK-UHFFFAOYSA-N 3-phenyl-1,3-oxazolidin-2-one Chemical class O=C1OCCN1C1=CC=CC=C1 NCTCGHLIHJJIBK-UHFFFAOYSA-N 0.000 title abstract description 9
- 239000004599 antimicrobial Substances 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 229910052731 fluorine Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 136
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 20
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- 229920006395 saturated elastomer Polymers 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- 150000003839 salts Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 7
- 208000015181 infectious disease Diseases 0.000 claims description 4
- JJBMTUJJQREOPY-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(triazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=NC=C2)C(F)=C1 JJBMTUJJQREOPY-NSHDSACASA-N 0.000 claims description 4
- ZVBWVLBBTKOCAK-VIFPVBQESA-N 2,2-dichloro-n-[[(5s)-3-[3-fluoro-4-(triazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound FC1=CC(N2C(O[C@@H](CNC(=O)C(Cl)Cl)C2)=O)=CC=C1N1C=CN=N1 ZVBWVLBBTKOCAK-VIFPVBQESA-N 0.000 claims description 3
- 229940079593 drug Drugs 0.000 claims description 3
- UMLNIWQBJGTETK-KRWDZBQOSA-N ethyl 3-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrol-3-yl]prop-2-enoate Chemical compound C1=C(C=CC(=O)OCC)C=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F UMLNIWQBJGTETK-KRWDZBQOSA-N 0.000 claims description 3
- VRWZPGHWWXLUNF-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(1,2,4-triazol-1-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=CN=C2)C(F)=C1 VRWZPGHWWXLUNF-NSHDSACASA-N 0.000 claims description 3
- NDGLBEXXAOLMOO-LBPRGKRZSA-N N-[[(5S)-3-[3-fluoro-4-[4-(N-hydroxy-C-methylcarbonimidoyl)triazol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=NC(=C2)C(C)=NO)C(F)=C1 NDGLBEXXAOLMOO-LBPRGKRZSA-N 0.000 claims description 2
- GTUBRVXIOOUIKJ-ZDUSSCGKSA-N N-[[(5S)-3-[3-fluoro-4-[4-(methoxyiminomethyl)triazol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound N1=NC(C=NOC)=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F GTUBRVXIOOUIKJ-ZDUSSCGKSA-N 0.000 claims description 2
- 230000000813 microbial effect Effects 0.000 claims description 2
- PNLNFJVPQDLGEZ-LBPRGKRZSA-N n-[[(5s)-3-(3-fluoro-4-imidazol-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=NC=C2)C(F)=C1 PNLNFJVPQDLGEZ-LBPRGKRZSA-N 0.000 claims description 2
- QOWOXBFFQOXPHM-UHFFFAOYSA-O oxo-[[1-[[4-(oxoazaniumylmethylidene)pyridin-1-yl]methyl]pyridin-4-ylidene]methyl]azanium;chloride Chemical compound [Cl-].C1=CC(=C[NH+]=O)C=CN1CN1C=CC(=C[NH+]=O)C=C1 QOWOXBFFQOXPHM-UHFFFAOYSA-O 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims 1
- -1 or O2CCH2N(CH3)2 Chemical group 0.000 abstract description 12
- 239000000460 chlorine Substances 0.000 abstract description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract description 7
- 125000002252 acyl group Chemical group 0.000 abstract description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract description 5
- 125000004423 acyloxy group Chemical group 0.000 abstract description 4
- 125000003545 alkoxy group Chemical group 0.000 abstract description 3
- 230000000845 anti-microbial effect Effects 0.000 abstract description 3
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract description 2
- 125000003282 alkyl amino group Chemical group 0.000 abstract description 2
- 125000004663 dialkyl amino group Chemical group 0.000 abstract description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract 2
- 239000011737 fluorine Substances 0.000 abstract 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 abstract 1
- 101100295741 Gallus gallus COR4 gene Proteins 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- 230000000063 preceeding effect Effects 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 216
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 210
- 239000000243 solution Substances 0.000 description 190
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 177
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 103
- 239000007787 solid Substances 0.000 description 102
- 239000000203 mixture Substances 0.000 description 78
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 78
- 239000011734 sodium Substances 0.000 description 58
- 238000001035 drying Methods 0.000 description 52
- 238000000034 method Methods 0.000 description 50
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 47
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 47
- 238000003756 stirring Methods 0.000 description 47
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 45
- 238000006243 chemical reaction Methods 0.000 description 37
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 32
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 31
- 238000010438 heat treatment Methods 0.000 description 31
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 30
- 239000002904 solvent Substances 0.000 description 29
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 28
- 239000000741 silica gel Substances 0.000 description 27
- 229910002027 silica gel Inorganic materials 0.000 description 27
- 150000001540 azides Chemical class 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
- 238000001819 mass spectrum Methods 0.000 description 24
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 21
- PXIPVTKHYLBLMZ-UHFFFAOYSA-N Sodium azide Chemical compound [Na+].[N-]=[N+]=[N-] PXIPVTKHYLBLMZ-UHFFFAOYSA-N 0.000 description 20
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical class [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 20
- 239000000706 filtrate Substances 0.000 description 19
- 238000005984 hydrogenation reaction Methods 0.000 description 18
- 239000000463 material Substances 0.000 description 18
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical class O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 description 17
- 239000012065 filter cake Substances 0.000 description 16
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 16
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 238000010992 reflux Methods 0.000 description 15
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 14
- 238000004587 chromatography analysis Methods 0.000 description 14
- 238000000605 extraction Methods 0.000 description 14
- 230000002829 reductive effect Effects 0.000 description 14
- 239000012044 organic layer Substances 0.000 description 13
- 238000010792 warming Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 12
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 12
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonium chloride Substances [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 11
- 239000002585 base Chemical class 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000012359 Methanesulfonyl chloride Substances 0.000 description 10
- 239000007868 Raney catalyst Substances 0.000 description 10
- 229910000564 Raney nickel Inorganic materials 0.000 description 10
- 241000700159 Rattus Species 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 10
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 10
- 150000001448 anilines Chemical class 0.000 description 9
- 238000010790 dilution Methods 0.000 description 9
- 239000012895 dilution Substances 0.000 description 9
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 9
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 8
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 8
- 229910000027 potassium carbonate Inorganic materials 0.000 description 8
- 239000011343 solid material Substances 0.000 description 8
- RUBQQRMAWLSCCJ-UHFFFAOYSA-N 1,2-difluoro-4-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=C(F)C(F)=C1 RUBQQRMAWLSCCJ-UHFFFAOYSA-N 0.000 description 7
- MHZGKXUYDGKKIU-UHFFFAOYSA-N Decylamine Chemical compound CCCCCCCCCCN MHZGKXUYDGKKIU-UHFFFAOYSA-N 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 7
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 7
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000001816 cooling Methods 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- 241001465754 Metazoa Species 0.000 description 6
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 6
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 6
- YLNSNVGRSIOCEU-ZCFIWIBFSA-N [(2r)-oxiran-2-yl]methyl butanoate Chemical compound CCCC(=O)OC[C@H]1CO1 YLNSNVGRSIOCEU-ZCFIWIBFSA-N 0.000 description 6
- 229960000583 acetic acid Drugs 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 239000003242 anti bacterial agent Substances 0.000 description 6
- 229910052799 carbon Inorganic materials 0.000 description 6
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 150000002828 nitro derivatives Chemical class 0.000 description 6
- 229910052697 platinum Inorganic materials 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- 239000002002 slurry Substances 0.000 description 6
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- UCKMPCXJQFINFW-UHFFFAOYSA-N Sulphide Chemical compound [S-2] UCKMPCXJQFINFW-UHFFFAOYSA-N 0.000 description 5
- 235000011114 ammonium hydroxide Nutrition 0.000 description 5
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 5
- OQNGCCWBHLEQFN-UHFFFAOYSA-N chloroform;hexane Chemical compound ClC(Cl)Cl.CCCCCC OQNGCCWBHLEQFN-UHFFFAOYSA-N 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
- GRWIABMEEKERFV-UHFFFAOYSA-N methanol;oxolane Chemical compound OC.C1CCOC1 GRWIABMEEKERFV-UHFFFAOYSA-N 0.000 description 5
- 239000000825 pharmaceutical preparation Substances 0.000 description 5
- 239000011541 reaction mixture Substances 0.000 description 5
- BGKABGGFJSTLIL-UHFFFAOYSA-N 3-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound OCN1CCOC1=O BGKABGGFJSTLIL-UHFFFAOYSA-N 0.000 description 4
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 4
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 4
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
- 229910052783 alkali metal Inorganic materials 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 239000000908 ammonium hydroxide Substances 0.000 description 4
- 230000000844 anti-bacterial effect Effects 0.000 description 4
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 4
- 230000037396 body weight Effects 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 150000002391 heterocyclic compounds Chemical class 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229910052763 palladium Inorganic materials 0.000 description 4
- 150000003233 pyrroles Chemical class 0.000 description 4
- 239000011780 sodium chloride Substances 0.000 description 4
- 239000012312 sodium hydride Substances 0.000 description 4
- 229910000104 sodium hydride Inorganic materials 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 4
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 4
- XEZNGIUYQVAUSS-UHFFFAOYSA-N 18-crown-6 Chemical compound C1COCCOCCOCCOCCOCCO1 XEZNGIUYQVAUSS-UHFFFAOYSA-N 0.000 description 3
- 206010003694 Atrophy Diseases 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- 239000012448 Lithium borohydride Substances 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 230000037444 atrophy Effects 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000013058 crude material Substances 0.000 description 3
- 229940111685 dibasic potassium phosphate Drugs 0.000 description 3
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 description 3
- OAYLNYINCPYISS-UHFFFAOYSA-N ethyl acetate;hexane Chemical compound CCCCCC.CCOC(C)=O OAYLNYINCPYISS-UHFFFAOYSA-N 0.000 description 3
- 239000012362 glacial acetic acid Substances 0.000 description 3
- 238000012986 modification Methods 0.000 description 3
- 230000004048 modification Effects 0.000 description 3
- 229910017604 nitric acid Inorganic materials 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 239000012279 sodium borohydride Substances 0.000 description 3
- 229910000033 sodium borohydride Inorganic materials 0.000 description 3
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 3
- 230000002110 toxicologic effect Effects 0.000 description 3
- 231100000027 toxicology Toxicity 0.000 description 3
- 230000009466 transformation Effects 0.000 description 3
- 238000000844 transformation Methods 0.000 description 3
- 150000003852 triazoles Chemical class 0.000 description 3
- 239000003981 vehicle Substances 0.000 description 3
- FQATYOLCQDPVAV-VIFPVBQESA-N (5r)-5-(azidomethyl)-3-[3-fluoro-4-(triazol-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(O[C@@H](CN=[N+]=[N-])C2)=O)=CC=C1N1C=CN=N1 FQATYOLCQDPVAV-VIFPVBQESA-N 0.000 description 2
- DKTQTONVJHTCIW-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)triazole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1N=NC=C1 DKTQTONVJHTCIW-UHFFFAOYSA-N 0.000 description 2
- HFFXLYHRNRKAPM-UHFFFAOYSA-N 2,4,5-trichloro-n-(5-methyl-1,2-oxazol-3-yl)benzenesulfonamide Chemical compound O1C(C)=CC(NS(=O)(=O)C=2C(=CC(Cl)=C(Cl)C=2)Cl)=N1 HFFXLYHRNRKAPM-UHFFFAOYSA-N 0.000 description 2
- JUVVIXJCRBLXIB-UHFFFAOYSA-N 2-(2-fluoro-4-nitrophenyl)triazole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1N=CC=N1 JUVVIXJCRBLXIB-UHFFFAOYSA-N 0.000 description 2
- RGUXEWWHSQGVRZ-UHFFFAOYSA-N 3,3-diethoxyprop-1-yne Chemical compound CCOC(C#C)OCC RGUXEWWHSQGVRZ-UHFFFAOYSA-N 0.000 description 2
- NHQDETIJWKXCTC-UHFFFAOYSA-N 3-chloroperbenzoic acid Chemical compound OOC(=O)C1=CC=CC(Cl)=C1 NHQDETIJWKXCTC-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- JXRGUPLJCCDGKG-UHFFFAOYSA-N 4-nitrobenzenesulfonyl chloride Chemical compound [O-][N+](=O)C1=CC=C(S(Cl)(=O)=O)C=C1 JXRGUPLJCCDGKG-UHFFFAOYSA-N 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 208000035143 Bacterial infection Diseases 0.000 description 2
- KZMGYPLQYOPHEL-UHFFFAOYSA-N Boron trifluoride etherate Chemical compound FB(F)F.CCOCC KZMGYPLQYOPHEL-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 241001112696 Clostridia Species 0.000 description 2
- GSNUFIFRDBKVIE-UHFFFAOYSA-N DMF Natural products CC1=CC=C(C)O1 GSNUFIFRDBKVIE-UHFFFAOYSA-N 0.000 description 2
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 2
- LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
- 241000699670 Mus sp. Species 0.000 description 2
- 241000186359 Mycobacterium Species 0.000 description 2
- 241000187479 Mycobacterium tuberculosis Species 0.000 description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
- 239000007832 Na2SO4 Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 2
- 241000295644 Staphylococcaceae Species 0.000 description 2
- 241000191967 Staphylococcus aureus Species 0.000 description 2
- GOPYZMJAIPBUGX-UHFFFAOYSA-N [O-2].[O-2].[Mn+4] Chemical class [O-2].[O-2].[Mn+4] GOPYZMJAIPBUGX-UHFFFAOYSA-N 0.000 description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 244000037640 animal pathogen Species 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 208000022362 bacterial infectious disease Diseases 0.000 description 2
- 230000036765 blood level Effects 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 210000001185 bone marrow Anatomy 0.000 description 2
- 210000004556 brain Anatomy 0.000 description 2
- 239000006172 buffering agent Substances 0.000 description 2
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 229940125782 compound 2 Drugs 0.000 description 2
- 238000007796 conventional method Methods 0.000 description 2
- DDRJAANPRJIHGJ-UHFFFAOYSA-N creatinine Chemical compound CN1CC(=O)NC1=N DDRJAANPRJIHGJ-UHFFFAOYSA-N 0.000 description 2
- 238000006193 diazotization reaction Methods 0.000 description 2
- UPPBZOFWXKFRHI-UHFFFAOYSA-N dichloromethane;hexane;methanol Chemical compound OC.ClCCl.CCCCCC UPPBZOFWXKFRHI-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 2
- 239000000796 flavoring agent Substances 0.000 description 2
- 235000013355 food flavoring agent Nutrition 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 244000052637 human pathogen Species 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- 239000011261 inert gas Substances 0.000 description 2
- 238000001802 infusion Methods 0.000 description 2
- 229910052744 lithium Inorganic materials 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
- GTCAXTIRRLKXRU-UHFFFAOYSA-N methyl carbamate Chemical compound COC(N)=O GTCAXTIRRLKXRU-UHFFFAOYSA-N 0.000 description 2
- 229920000609 methyl cellulose Polymers 0.000 description 2
- XMJHPCRAQCTCFT-UHFFFAOYSA-N methyl chloroformate Chemical compound COC(Cl)=O XMJHPCRAQCTCFT-UHFFFAOYSA-N 0.000 description 2
- 239000001923 methylcellulose Substances 0.000 description 2
- SZUMFVZQOVYYHM-INIZCTEOSA-N n-[[(5s)-3-(3-fluoro-4-indol-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C3=CC=CC=C3C=C2)C(F)=C1 SZUMFVZQOVYYHM-INIZCTEOSA-N 0.000 description 2
- ANKSMUOKEFMQID-LBPRGKRZSA-N n-[[(5s)-3-(3-fluoro-4-pyrazol-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=CC=C2)C(F)=C1 ANKSMUOKEFMQID-LBPRGKRZSA-N 0.000 description 2
- GEUNXDRAMBSLSX-ZDUSSCGKSA-N n-[[(5s)-3-(3-fluoro-4-pyrrol-1-ylphenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=CC=C2)C(F)=C1 GEUNXDRAMBSLSX-ZDUSSCGKSA-N 0.000 description 2
- QNQPNMBRVDZPBY-JTQLQIEISA-N n-[[(5s)-3-[3-fluoro-4-(5-sulfanylidene-1h-1,2,4-triazol-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C(=NN=C2)S)C(F)=C1 QNQPNMBRVDZPBY-JTQLQIEISA-N 0.000 description 2
- BBDKNCCHNMTYCK-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(triazol-2-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=CC=N2)C(F)=C1 BBDKNCCHNMTYCK-NSHDSACASA-N 0.000 description 2
- FSSGFBIJCNRPNF-ZDUSSCGKSA-N n-[[(5s)-3-[3-fluoro-4-[4-(hydroxymethyl)pyrazol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=CC(CO)=C2)C(F)=C1 FSSGFBIJCNRPNF-ZDUSSCGKSA-N 0.000 description 2
- CIQMVCYQRWSVRR-LBPRGKRZSA-N n-[[(5s)-3-[4-(4-acetyltriazol-1-yl)-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=NC(=C2)C(C)=O)C(F)=C1 CIQMVCYQRWSVRR-LBPRGKRZSA-N 0.000 description 2
- 150000005181 nitrobenzenes Chemical class 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- BSCHIACBONPEOB-UHFFFAOYSA-N oxolane;hydrate Chemical compound O.C1CCOC1 BSCHIACBONPEOB-UHFFFAOYSA-N 0.000 description 2
- 238000007911 parenteral administration Methods 0.000 description 2
- 150000003018 phosphorus compounds Chemical class 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 229940068968 polysorbate 80 Drugs 0.000 description 2
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- JQWHASGSAFIOCM-UHFFFAOYSA-M sodium periodate Chemical compound [Na+].[O-]I(=O)(=O)=O JQWHASGSAFIOCM-UHFFFAOYSA-M 0.000 description 2
- 229910052938 sodium sulfate Inorganic materials 0.000 description 2
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
- 235000011152 sodium sulphate Nutrition 0.000 description 2
- 241000894007 species Species 0.000 description 2
- 210000000952 spleen Anatomy 0.000 description 2
- 238000013223 sprague-dawley female rat Methods 0.000 description 2
- 238000013222 sprague-dawley male rat Methods 0.000 description 2
- 238000012453 sprague-dawley rat model Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- 150000003871 sulfonates Chemical class 0.000 description 2
- 150000003457 sulfones Chemical class 0.000 description 2
- 239000003826 tablet Substances 0.000 description 2
- 238000010998 test method Methods 0.000 description 2
- 210000001541 thymus gland Anatomy 0.000 description 2
- 230000004580 weight loss Effects 0.000 description 2
- TXUICONDJPYNPY-UHFFFAOYSA-N (1,10,13-trimethyl-3-oxo-4,5,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl) heptanoate Chemical compound C1CC2CC(=O)C=C(C)C2(C)C2C1C1CCC(OC(=O)CCCCCC)C1(C)CC2 TXUICONDJPYNPY-UHFFFAOYSA-N 0.000 description 1
- WWTBZEKOSBFBEM-SPWPXUSOSA-N (2s)-2-[[2-benzyl-3-[hydroxy-[(1r)-2-phenyl-1-(phenylmethoxycarbonylamino)ethyl]phosphoryl]propanoyl]amino]-3-(1h-indol-3-yl)propanoic acid Chemical compound N([C@@H](CC=1C2=CC=CC=C2NC=1)C(=O)O)C(=O)C(CP(O)(=O)[C@H](CC=1C=CC=CC=1)NC(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 WWTBZEKOSBFBEM-SPWPXUSOSA-N 0.000 description 1
- MRVFOEIHWLDLIJ-VIFPVBQESA-N (5R)-5-(azidomethyl)-3-[3-fluoro-4-(triazol-2-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound Fc1cc(ccc1-n1nccn1)N1C[C@H](CN=[N+]=[N-])OC1=O MRVFOEIHWLDLIJ-VIFPVBQESA-N 0.000 description 1
- YYAOSPUCVYFFPN-SNVBAGLBSA-N (5S)-5-(azidomethyl)-3-(3-fluoro-4-imidazol-1-ylphenyl)-1,3-oxazolidin-2-one Chemical compound FC=1C=C(C=CC=1N1C=NC=C1)N1C(O[C@@H](C1)CN=[N+]=[N-])=O YYAOSPUCVYFFPN-SNVBAGLBSA-N 0.000 description 1
- PUWJHWTZUZWDTR-SNVBAGLBSA-N (5S)-5-(azidomethyl)-3-(3-fluoro-4-pyrazol-1-ylphenyl)-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(O[C@H](CN=[N+]=[N-])C2)=O)=CC=C1N1C=CC=N1 PUWJHWTZUZWDTR-SNVBAGLBSA-N 0.000 description 1
- IFUHPDNSCBSJOV-LLVKDONJSA-N (5S)-5-(azidomethyl)-3-(3-fluoro-4-pyrrol-1-ylphenyl)-1,3-oxazolidin-2-one Chemical compound FC1=CC(N2C(O[C@H](CN=[N+]=[N-])C2)=O)=CC=C1N1C=CC=C1 IFUHPDNSCBSJOV-LLVKDONJSA-N 0.000 description 1
- DDZHNEQAFVSJMJ-SECBINFHSA-N (5S)-5-(azidomethyl)-3-[3-fluoro-4-(1,2,4-triazol-1-yl)phenyl]-1,3-oxazolidin-2-one Chemical compound FC=1C=C(C=CC=1N1N=CN=C1)N1C(O[C@@H](C1)CN=[N+]=[N-])=O DDZHNEQAFVSJMJ-SECBINFHSA-N 0.000 description 1
- XJZBQOZESUTBMG-SECBINFHSA-N (5r)-3-[3-fluoro-4-(triazol-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2N=NC=C2)C(F)=C1 XJZBQOZESUTBMG-SECBINFHSA-N 0.000 description 1
- QRVCIFFMQGQXNC-SECBINFHSA-N (5r)-3-[3-fluoro-4-(triazol-2-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2N=CC=N2)C(F)=C1 QRVCIFFMQGQXNC-SECBINFHSA-N 0.000 description 1
- HEGFBNZPTKHZDT-NNJIEVJOSA-N (5r)-3-[3-fluoro-4-[4-(oxan-2-yloxymethyl)pyrazol-1-yl]phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@@H](CO)CN1C1=CC=C(N2N=CC(COC3OCCCC3)=C2)C(F)=C1 HEGFBNZPTKHZDT-NNJIEVJOSA-N 0.000 description 1
- ALPUBWSOWJVBBL-JTQLQIEISA-N (5s)-3-(3-fluoro-4-imidazol-1-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=CC=C(N2C=NC=C2)C(F)=C1 ALPUBWSOWJVBBL-JTQLQIEISA-N 0.000 description 1
- GJGVMBKNNZXXJH-JTQLQIEISA-N (5s)-3-(3-fluoro-4-pyrazol-1-ylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=CC=C(N2N=CC=C2)C(F)=C1 GJGVMBKNNZXXJH-JTQLQIEISA-N 0.000 description 1
- OJXYLZGQGNQXAF-VIFPVBQESA-N (5s)-3-[3-fluoro-4-(1,2,4-triazol-1-yl)phenyl]-5-(hydroxymethyl)-1,3-oxazolidin-2-one Chemical compound O=C1O[C@H](CO)CN1C1=CC=C(N2N=CN=C2)C(F)=C1 OJXYLZGQGNQXAF-VIFPVBQESA-N 0.000 description 1
- SBGIVOCRFORXTD-CQSZACIVSA-N (5s)-5-(azidomethyl)-3-(3-fluoro-4-indol-1-ylphenyl)-1,3-oxazolidin-2-one Chemical compound C=1C=C(N2C3=CC=CC=C3C=C2)C(F)=CC=1N1C[C@@H](CN=[N+]=[N-])OC1=O SBGIVOCRFORXTD-CQSZACIVSA-N 0.000 description 1
- DAXJNUBSBFUTRP-RTQNCGMRSA-N (8r,9s,10r,13s,14s)-6-(hydroxymethyl)-10,13-dimethyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-3,17-dione Chemical compound O=C1C=C[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CC(CO)C2=C1 DAXJNUBSBFUTRP-RTQNCGMRSA-N 0.000 description 1
- MIOPJNTWMNEORI-GMSGAONNSA-N (S)-camphorsulfonic acid Chemical compound C1C[C@@]2(CS(O)(=O)=O)C(=O)C[C@@H]1C2(C)C MIOPJNTWMNEORI-GMSGAONNSA-N 0.000 description 1
- IXIJRPBFPLESEI-UHFFFAOYSA-N 1,2-difluoro-3-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC(F)=C1F IXIJRPBFPLESEI-UHFFFAOYSA-N 0.000 description 1
- JTOQNQIBUCTGFM-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)-1,2,4-triazole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1N=CN=C1 JTOQNQIBUCTGFM-UHFFFAOYSA-N 0.000 description 1
- SPRGMIFFQVXJSZ-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)imidazole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1C=NC=C1 SPRGMIFFQVXJSZ-UHFFFAOYSA-N 0.000 description 1
- JRAGWAJQPORJFQ-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)indole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1C2=CC=CC=C2C=C1 JRAGWAJQPORJFQ-UHFFFAOYSA-N 0.000 description 1
- YNYHDGYGCYUVOE-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)pyrazole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1N=CC=C1 YNYHDGYGCYUVOE-UHFFFAOYSA-N 0.000 description 1
- ZDXGNQAJKPPTHC-UHFFFAOYSA-N 1-(2-fluoro-4-nitrophenyl)pyrrole Chemical compound FC1=CC([N+](=O)[O-])=CC=C1N1C=CC=C1 ZDXGNQAJKPPTHC-UHFFFAOYSA-N 0.000 description 1
- UNILWMWFPHPYOR-KXEYIPSPSA-M 1-[6-[2-[3-[3-[3-[2-[2-[3-[[2-[2-[[(2r)-1-[[2-[[(2r)-1-[3-[2-[2-[3-[[2-(2-amino-2-oxoethoxy)acetyl]amino]propoxy]ethoxy]ethoxy]propylamino]-3-hydroxy-1-oxopropan-2-yl]amino]-2-oxoethyl]amino]-3-[(2r)-2,3-di(hexadecanoyloxy)propyl]sulfanyl-1-oxopropan-2-yl Chemical compound O=C1C(SCCC(=O)NCCCOCCOCCOCCCNC(=O)COCC(=O)N[C@@H](CSC[C@@H](COC(=O)CCCCCCCCCCCCCCC)OC(=O)CCCCCCCCCCCCCCC)C(=O)NCC(=O)N[C@H](CO)C(=O)NCCCOCCOCCOCCCNC(=O)COCC(N)=O)CC(=O)N1CCNC(=O)CCCCCN\1C2=CC=C(S([O-])(=O)=O)C=C2CC/1=C/C=C/C=C/C1=[N+](CC)C2=CC=C(S([O-])(=O)=O)C=C2C1 UNILWMWFPHPYOR-KXEYIPSPSA-M 0.000 description 1
- QWENRTYMTSOGBR-UHFFFAOYSA-N 1H-1,2,3-Triazole Chemical compound C=1C=NNN=1 QWENRTYMTSOGBR-UHFFFAOYSA-N 0.000 description 1
- LRGBDJBDJXZTTD-UHFFFAOYSA-N 1h-pyrazole-4-carbaldehyde Chemical compound O=CC=1C=NNC=1 LRGBDJBDJXZTTD-UHFFFAOYSA-N 0.000 description 1
- KORIJXKQGMTQTO-UHFFFAOYSA-N 1h-pyrrol-2-ylmethanol Chemical compound OCC1=CC=CN1 KORIJXKQGMTQTO-UHFFFAOYSA-N 0.000 description 1
- CHNYVNOFAWYUEG-UHFFFAOYSA-N 1h-pyrrole-3-carbaldehyde Chemical compound O=CC=1C=CNC=1 CHNYVNOFAWYUEG-UHFFFAOYSA-N 0.000 description 1
- QMIGEDXMDGEZSR-UHFFFAOYSA-N 2,5-dimethoxyoxolane-3-carbaldehyde Chemical compound COC1CC(C=O)C(OC)O1 QMIGEDXMDGEZSR-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- NOIXNOMHHWGUTG-UHFFFAOYSA-N 2-[[4-[4-pyridin-4-yl-1-(2,2,2-trifluoroethyl)pyrazol-3-yl]phenoxy]methyl]quinoline Chemical class C=1C=C(OCC=2N=C3C=CC=CC3=CC=2)C=CC=1C1=NN(CC(F)(F)F)C=C1C1=CC=NC=C1 NOIXNOMHHWGUTG-UHFFFAOYSA-N 0.000 description 1
- AVFCIVAVZHKRQO-UHFFFAOYSA-N 3,5-dimethoxyoxolane-3-carbaldehyde Chemical compound COC1CC(C=O)(OC)CO1 AVFCIVAVZHKRQO-UHFFFAOYSA-N 0.000 description 1
- VZQVLZBWWQBKFP-UHFFFAOYSA-N 3-fluoro-4-(1,2,4-triazol-1-yl)aniline Chemical compound FC1=CC(N)=CC=C1N1N=CN=C1 VZQVLZBWWQBKFP-UHFFFAOYSA-N 0.000 description 1
- IMBBXSASDSZJSX-UHFFFAOYSA-N 4-Carboxypyrazole Chemical compound OC(=O)C=1C=NNC=1 IMBBXSASDSZJSX-UHFFFAOYSA-N 0.000 description 1
- SPXOTSHWBDUUMT-UHFFFAOYSA-M 4-nitrobenzenesulfonate Chemical compound [O-][N+](=O)C1=CC=C(S([O-])(=O)=O)C=C1 SPXOTSHWBDUUMT-UHFFFAOYSA-M 0.000 description 1
- NSPMIYGKQJPBQR-UHFFFAOYSA-N 4H-1,2,4-triazole Chemical compound C=1N=CNN=1 NSPMIYGKQJPBQR-UHFFFAOYSA-N 0.000 description 1
- HBAQYPYDRFILMT-UHFFFAOYSA-N 8-[3-(1-cyclopropylpyrazol-4-yl)-1H-pyrazolo[4,3-d]pyrimidin-5-yl]-3-methyl-3,8-diazabicyclo[3.2.1]octan-2-one Chemical class C1(CC1)N1N=CC(=C1)C1=NNC2=C1N=C(N=C2)N1C2C(N(CC1CC2)C)=O HBAQYPYDRFILMT-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 201000004384 Alopecia Diseases 0.000 description 1
- 208000037157 Azotemia Diseases 0.000 description 1
- 241001148536 Bacteroides sp. Species 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 102000004506 Blood Proteins Human genes 0.000 description 1
- 108010017384 Blood Proteins Proteins 0.000 description 1
- 206010006895 Cachexia Diseases 0.000 description 1
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 1
- 239000004375 Dextrin Substances 0.000 description 1
- 229920001353 Dextrin Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- BWGNESOTFCXPMA-UHFFFAOYSA-N Dihydrogen disulfide Chemical compound SS BWGNESOTFCXPMA-UHFFFAOYSA-N 0.000 description 1
- BUDQDWGNQVEFAC-UHFFFAOYSA-N Dihydropyran Chemical compound C1COC=CC1 BUDQDWGNQVEFAC-UHFFFAOYSA-N 0.000 description 1
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 description 1
- 241000192125 Firmicutes Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 238000006736 Huisgen cycloaddition reaction Methods 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 1
- 206010020565 Hyperaemia Diseases 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- ODKSFYDXXFIFQN-BYPYZUCNSA-N L-arginine Chemical compound OC(=O)[C@@H](N)CCCN=C(N)N ODKSFYDXXFIFQN-BYPYZUCNSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- 206010025327 Lymphopenia Diseases 0.000 description 1
- 208000002720 Malnutrition Diseases 0.000 description 1
- 241001529936 Murinae Species 0.000 description 1
- 241000186367 Mycobacterium avium Species 0.000 description 1
- MBBZMMPHUWSWHV-BDVNFPICSA-N N-methylglucamine Chemical compound CNC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO MBBZMMPHUWSWHV-BDVNFPICSA-N 0.000 description 1
- NFGCHPOPAAGIIM-AWEZNQCLSA-N O=C1O[C@H](CO)CN1C1=CC=C(N2C3=CC=CC=C3C=C2)C(F)=C1 Chemical compound O=C1O[C@H](CO)CN1C1=CC=C(N2C3=CC=CC=C3C=C2)C(F)=C1 NFGCHPOPAAGIIM-AWEZNQCLSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 206010033661 Pancytopenia Diseases 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- 235000014680 Saccharomyces cerevisiae Nutrition 0.000 description 1
- 102000007562 Serum Albumin Human genes 0.000 description 1
- 108010071390 Serum Albumin Proteins 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 241000193998 Streptococcus pneumoniae Species 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 229910021626 Tin(II) chloride Inorganic materials 0.000 description 1
- 108010059993 Vancomycin Proteins 0.000 description 1
- 241000748245 Villanova Species 0.000 description 1
- PNNCWTXUWKENPE-UHFFFAOYSA-N [N].NC(N)=O Chemical compound [N].NC(N)=O PNNCWTXUWKENPE-UHFFFAOYSA-N 0.000 description 1
- AUALQMFGWLZREY-UHFFFAOYSA-N acetonitrile;methanol Chemical compound OC.CC#N AUALQMFGWLZREY-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 150000000475 acetylene derivatives Chemical class 0.000 description 1
- 238000007171 acid catalysis Methods 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000001154 acute effect Effects 0.000 description 1
- 239000002671 adjuvant Substances 0.000 description 1
- 210000004404 adrenal cortex Anatomy 0.000 description 1
- 210000004100 adrenal gland Anatomy 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 241001148470 aerobic bacillus Species 0.000 description 1
- 238000002814 agar dilution Methods 0.000 description 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 231100000360 alopecia Toxicity 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 208000007502 anemia Diseases 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 238000009635 antibiotic susceptibility testing Methods 0.000 description 1
- 239000000010 aprotic solvent Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- SRSXLGNVWSONIS-UHFFFAOYSA-N benzenesulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1 SRSXLGNVWSONIS-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- KCXMKQUNVWSEMD-UHFFFAOYSA-N benzyl chloride Chemical compound ClCC1=CC=CC=C1 KCXMKQUNVWSEMD-UHFFFAOYSA-N 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- UFWKEJACGOZAAL-UHFFFAOYSA-N benzyl n-(3-fluoro-4-imidazol-1-ylphenyl)carbamate Chemical compound C=1C=C(N2C=NC=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 UFWKEJACGOZAAL-UHFFFAOYSA-N 0.000 description 1
- BFUPFBCYIXRBJT-UHFFFAOYSA-N benzyl n-(3-fluoro-4-indol-1-ylphenyl)carbamate Chemical compound C=1C=C(N2C3=CC=CC=C3C=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 BFUPFBCYIXRBJT-UHFFFAOYSA-N 0.000 description 1
- WQNJMGLUSLSCMB-UHFFFAOYSA-N benzyl n-(3-fluoro-4-pyrazol-1-ylphenyl)carbamate Chemical compound C=1C=C(N2N=CC=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 WQNJMGLUSLSCMB-UHFFFAOYSA-N 0.000 description 1
- IHPGABPMYRBPMG-UHFFFAOYSA-N benzyl n-(3-fluoro-4-pyrrol-1-ylphenyl)carbamate Chemical compound C=1C=C(N2C=CC=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 IHPGABPMYRBPMG-UHFFFAOYSA-N 0.000 description 1
- OEVKNDAZGWHFOP-UHFFFAOYSA-N benzyl n-[3-fluoro-4-(1,2,4-triazol-1-yl)phenyl]carbamate Chemical compound C=1C=C(N2N=CN=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 OEVKNDAZGWHFOP-UHFFFAOYSA-N 0.000 description 1
- KTAGRURQLUKSRH-UHFFFAOYSA-N benzyl n-[3-fluoro-4-(triazol-1-yl)phenyl]carbamate Chemical compound C=1C=C(N2N=NC=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 KTAGRURQLUKSRH-UHFFFAOYSA-N 0.000 description 1
- IXJIEOKKXKNKMY-UHFFFAOYSA-N benzyl n-[3-fluoro-4-(triazol-2-yl)phenyl]carbamate Chemical compound C=1C=C(N2N=CC=N2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 IXJIEOKKXKNKMY-UHFFFAOYSA-N 0.000 description 1
- WKXHTWOOAGMLHQ-UHFFFAOYSA-N benzyl n-[3-fluoro-4-[4-(hydroxymethyl)pyrazol-1-yl]phenyl]carbamate Chemical compound C1=C(CO)C=NN1C(C(=C1)F)=CC=C1NC(=O)OCC1=CC=CC=C1 WKXHTWOOAGMLHQ-UHFFFAOYSA-N 0.000 description 1
- QVVAVDQHEBSAPF-UHFFFAOYSA-N benzyl n-[3-fluoro-4-[4-(oxan-2-yloxymethyl)pyrazol-1-yl]phenyl]carbamate Chemical compound C=1C=C(N2N=CC(COC3OCCCC3)=C2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 QVVAVDQHEBSAPF-UHFFFAOYSA-N 0.000 description 1
- UZDMJQDCIQJVOQ-QHCPKHFHSA-N benzyl n-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]-n-benzylcarbamate Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N(C(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 UZDMJQDCIQJVOQ-QHCPKHFHSA-N 0.000 description 1
- WJELIXPICFIQOP-UHFFFAOYSA-N benzyl n-benzyl-n-[2-fluoro-4-(phenylmethoxycarbonylamino)phenyl]carbamate Chemical compound C=1C=C(N(CC=2C=CC=CC=2)C(=O)OCC=2C=CC=CC=2)C(F)=CC=1NC(=O)OCC1=CC=CC=C1 WJELIXPICFIQOP-UHFFFAOYSA-N 0.000 description 1
- HBOJXMDMTFTVTQ-OAQYLSRUSA-N benzyl n-benzyl-n-[2-fluoro-4-[(5r)-5-(hydroxymethyl)-2-oxo-1,3-oxazolidin-3-yl]phenyl]carbamate Chemical compound O=C1O[C@@H](CO)CN1C(C=C1F)=CC=C1N(C(=O)OCC=1C=CC=CC=1)CC1=CC=CC=C1 HBOJXMDMTFTVTQ-OAQYLSRUSA-N 0.000 description 1
- 150000005347 biaryls Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 230000036760 body temperature Effects 0.000 description 1
- UWTDFICHZKXYAC-UHFFFAOYSA-N boron;oxolane Chemical compound [B].C1CCOC1 UWTDFICHZKXYAC-UHFFFAOYSA-N 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- XRGPFNGLRSIPSA-UHFFFAOYSA-N butyn-2-one Chemical compound CC(=O)C#C XRGPFNGLRSIPSA-UHFFFAOYSA-N 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 210000004534 cecum Anatomy 0.000 description 1
- KXZJHVJKXJLBKO-UHFFFAOYSA-N chembl1408157 Chemical compound N=1C2=CC=CC=C2C(C(=O)O)=CC=1C1=CC=C(O)C=C1 KXZJHVJKXJLBKO-UHFFFAOYSA-N 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000007979 citrate buffer Substances 0.000 description 1
- 229940110456 cocoa butter Drugs 0.000 description 1
- 235000019868 cocoa butter Nutrition 0.000 description 1
- 229940125810 compound 20 Drugs 0.000 description 1
- 229940126208 compound 22 Drugs 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 229940127271 compound 49 Drugs 0.000 description 1
- 208000027744 congestion Diseases 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- 229940109239 creatinine Drugs 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000006352 cycloaddition reaction Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- HCAJEUSONLESMK-UHFFFAOYSA-N cyclohexylsulfamic acid Chemical class OS(=O)(=O)NC1CCCCC1 HCAJEUSONLESMK-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 235000019425 dextrin Nutrition 0.000 description 1
- 125000005331 diazinyl group Chemical group N1=NC(=CC=C1)* 0.000 description 1
- 239000012954 diazonium Substances 0.000 description 1
- 150000001989 diazonium salts Chemical class 0.000 description 1
- NTBIYBAYFBNTCD-UHFFFAOYSA-N dibenzoyl 2,3-dihydroxybutanedioate Chemical compound C=1C=CC=CC=1C(=O)OC(=O)C(O)C(O)C(=O)OC(=O)C1=CC=CC=C1 NTBIYBAYFBNTCD-UHFFFAOYSA-N 0.000 description 1
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 229910001882 dioxygen Inorganic materials 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003937 drug carrier Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 208000026500 emaciation Diseases 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 239000003256 environmental substance Substances 0.000 description 1
- 210000003743 erythrocyte Anatomy 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- CCIVGXIOQKPBKL-UHFFFAOYSA-N ethanesulfonic acid Chemical class CCS(O)(=O)=O CCIVGXIOQKPBKL-UHFFFAOYSA-N 0.000 description 1
- SRCZQMGIVIYBBJ-UHFFFAOYSA-N ethoxyethane;ethyl acetate Chemical compound CCOCC.CCOC(C)=O SRCZQMGIVIYBBJ-UHFFFAOYSA-N 0.000 description 1
- MSPOSRHJXMILNK-UHFFFAOYSA-N ethyl 1h-pyrazole-5-carboxylate Chemical compound CCOC(=O)C1=CC=NN1 MSPOSRHJXMILNK-UHFFFAOYSA-N 0.000 description 1
- YZEWJYIDAAGEHA-UHFFFAOYSA-N ethyl 2-di(propan-2-yloxy)phosphorylacetate Chemical compound CCOC(=O)CP(=O)(OC(C)C)OC(C)C YZEWJYIDAAGEHA-UHFFFAOYSA-N 0.000 description 1
- GFJARXIJZLTSOY-KRWDZBQOSA-N ethyl 3-[1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrol-3-yl]propanoate Chemical compound C1=C(CCC(=O)OCC)C=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F GFJARXIJZLTSOY-KRWDZBQOSA-N 0.000 description 1
- XLAFUVPFOSIKFG-UHFFFAOYSA-N ethyl 4-methoxy-2-oxobut-3-enoate Chemical compound CCOC(=O)C(=O)C=COC XLAFUVPFOSIKFG-UHFFFAOYSA-N 0.000 description 1
- AZLPEJUVWWGLHA-UHFFFAOYSA-N ethyl acetate;hexane;methanol Chemical compound OC.CCCCCC.CCOC(C)=O AZLPEJUVWWGLHA-UHFFFAOYSA-N 0.000 description 1
- UREBWPXBXRYXRJ-UHFFFAOYSA-N ethyl acetate;methanol Chemical compound OC.CCOC(C)=O UREBWPXBXRYXRJ-UHFFFAOYSA-N 0.000 description 1
- 235000012631 food intake Nutrition 0.000 description 1
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical class [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 210000001156 gastric mucosa Anatomy 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 230000024924 glomerular filtration Effects 0.000 description 1
- 239000003862 glucocorticoid Substances 0.000 description 1
- 210000002175 goblet cell Anatomy 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000002489 hematologic effect Effects 0.000 description 1
- KDCIHNCMPUBDKT-UHFFFAOYSA-N hexane;propan-2-one Chemical compound CC(C)=O.CCCCCC KDCIHNCMPUBDKT-UHFFFAOYSA-N 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- 238000007327 hydrogenolysis reaction Methods 0.000 description 1
- XNXVOSBNFZWHBV-UHFFFAOYSA-N hydron;o-methylhydroxylamine;chloride Chemical compound Cl.CON XNXVOSBNFZWHBV-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- RCBVKBFIWMOMHF-UHFFFAOYSA-L hydroxy-(hydroxy(dioxo)chromio)oxy-dioxochromium;pyridine Chemical compound C1=CC=NC=C1.C1=CC=NC=C1.O[Cr](=O)(=O)O[Cr](O)(=O)=O RCBVKBFIWMOMHF-UHFFFAOYSA-L 0.000 description 1
- 238000007031 hydroxymethylation reaction Methods 0.000 description 1
- 210000003405 ileum Anatomy 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 238000000338 in vitro Methods 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010253 intravenous injection Methods 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000000644 isotonic solution Substances 0.000 description 1
- 210000003734 kidney Anatomy 0.000 description 1
- 229940001447 lactate Drugs 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 230000003902 lesion Effects 0.000 description 1
- 239000011968 lewis acid catalyst Substances 0.000 description 1
- TYZROVQLWOKYKF-ZDUSSCGKSA-N linezolid Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C(C=C1F)=CC=C1N1CCOCC1 TYZROVQLWOKYKF-ZDUSSCGKSA-N 0.000 description 1
- 239000008297 liquid dosage form Substances 0.000 description 1
- 210000004185 liver Anatomy 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 231100001023 lymphopenia Toxicity 0.000 description 1
- 229960003646 lysine Drugs 0.000 description 1
- ZLNQQNXFFQJAID-UHFFFAOYSA-L magnesium carbonate Chemical compound [Mg+2].[O-]C([O-])=O ZLNQQNXFFQJAID-UHFFFAOYSA-L 0.000 description 1
- 239000001095 magnesium carbonate Substances 0.000 description 1
- 229910000021 magnesium carbonate Inorganic materials 0.000 description 1
- 235000019359 magnesium stearate Nutrition 0.000 description 1
- 229940049920 malate Drugs 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N malic acid Chemical compound OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 230000001071 malnutrition Effects 0.000 description 1
- 235000000824 malnutrition Nutrition 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-M methanesulfonate group Chemical class CS(=O)(=O)[O-] AFVFQIVMOAPDHO-UHFFFAOYSA-M 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- WRWNFZAKUHZONV-UHFFFAOYSA-N methanetricarbaldehyde Chemical compound O=CC(C=O)C=O WRWNFZAKUHZONV-UHFFFAOYSA-N 0.000 description 1
- BKGMWZUAQIPLRV-UHFFFAOYSA-N methyl 1-[2-fluoro-4-(phenylmethoxycarbonylamino)phenyl]pyrazole-4-carboxylate Chemical compound C1=C(C(=O)OC)C=NN1C(C(=C1)F)=CC=C1NC(=O)OCC1=CC=CC=C1 BKGMWZUAQIPLRV-UHFFFAOYSA-N 0.000 description 1
- KJXBJLNJGUCQFH-AWEZNQCLSA-N methyl 1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]pyrrole-3-carboxylate Chemical compound C1=C(C(=O)OC)C=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F KJXBJLNJGUCQFH-AWEZNQCLSA-N 0.000 description 1
- XWXKPRXCAKXAEW-NSHDSACASA-N methyl 1-[4-[(5s)-5-(acetamidomethyl)-2-oxo-1,3-oxazolidin-3-yl]-2-fluorophenyl]triazole-4-carboxylate Chemical compound N1=NC(C(=O)OC)=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F XWXKPRXCAKXAEW-NSHDSACASA-N 0.000 description 1
- YSVFFMWRVMFEIW-UHFFFAOYSA-N methyl 1h-pyrazole-5-carboxylate;hydrochloride Chemical compound Cl.COC(=O)C=1C=CNN=1 YSVFFMWRVMFEIW-UHFFFAOYSA-N 0.000 description 1
- IMAKHNTVDGLIRY-UHFFFAOYSA-N methyl prop-2-ynoate Chemical compound COC(=O)C#C IMAKHNTVDGLIRY-UHFFFAOYSA-N 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000004660 morphological change Effects 0.000 description 1
- BJPWDHVQSSNHDV-LBPRGKRZSA-N n-[(5s)-3-(3-fluoro-4-isothiocyanatophenyl)-2-oxo-1,3-oxazolidin-5-yl]propanamide Chemical compound O=C1O[C@H](NC(=O)CC)CN1C1=CC=C(N=C=S)C(F)=C1 BJPWDHVQSSNHDV-LBPRGKRZSA-N 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- UXILYOUWGWHMFR-VIFPVBQESA-N n-[[(5s)-3-(4-amino-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N)C(F)=C1 UXILYOUWGWHMFR-VIFPVBQESA-N 0.000 description 1
- FZNDEYPBPQTOOI-VIFPVBQESA-N n-[[(5s)-3-(4-azido-3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N=[N+]=[N-])C(F)=C1 FZNDEYPBPQTOOI-VIFPVBQESA-N 0.000 description 1
- MKGUGOODDDZQRV-NSHDSACASA-N n-[[(5s)-3-[3-fluoro-4-(3-methylsulfanyl-1,2,4-triazol-4-yl)phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound CSC1=NN=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F MKGUGOODDDZQRV-NSHDSACASA-N 0.000 description 1
- JTHYLLDLECCIGA-INIZCTEOSA-N n-[[(5s)-3-[3-fluoro-4-[3-(3-hydroxypropyl)pyrrol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=C(CCCO)C=C2)C(F)=C1 JTHYLLDLECCIGA-INIZCTEOSA-N 0.000 description 1
- LUVHGRNPRGQJBT-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[3-(hydroxyiminomethyl)pyrrol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=C(C=NO)C=C2)C(F)=C1 LUVHGRNPRGQJBT-AWEZNQCLSA-N 0.000 description 1
- BKRIBYFSJUKDAW-AWEZNQCLSA-N n-[[(5s)-3-[3-fluoro-4-[3-(hydroxymethyl)pyrrol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=C(CO)C=C2)C(F)=C1 BKRIBYFSJUKDAW-AWEZNQCLSA-N 0.000 description 1
- FWBWFAIOWVGAMX-KRWDZBQOSA-N n-[[(5s)-3-[3-fluoro-4-[3-[3-(methanesulfonamido)propyl]pyrrol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2C=C(CCCNS(C)(=O)=O)C=C2)C(F)=C1 FWBWFAIOWVGAMX-KRWDZBQOSA-N 0.000 description 1
- CDFQYFSREHAJCP-ACGXKRRESA-N n-[[(5s)-3-[3-fluoro-4-[4-(1-hydroxyethyl)triazol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound N1=NC(C(O)C)=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F CDFQYFSREHAJCP-ACGXKRRESA-N 0.000 description 1
- ZPDZVOJLHAJASY-DIMJTDRSSA-N n-[[(5s)-3-[3-fluoro-4-[4-(oxan-2-yloxymethyl)pyrazol-1-yl]phenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound O=C1O[C@@H](CNC(=O)C)CN1C1=CC=C(N2N=CC(COC3OCCCC3)=C2)C(F)=C1 ZPDZVOJLHAJASY-DIMJTDRSSA-N 0.000 description 1
- IXUDVGJMRTYCCF-AWEZNQCLSA-N n-[[(5s)-3-[4-[4-(diethoxymethyl)triazol-1-yl]-3-fluorophenyl]-2-oxo-1,3-oxazolidin-5-yl]methyl]acetamide Chemical compound N1=NC(C(OCC)OCC)=CN1C1=CC=C(N2C(O[C@@H](CNC(C)=O)C2)=O)C=C1F IXUDVGJMRTYCCF-AWEZNQCLSA-N 0.000 description 1
- NTPGVWDPQFFUSU-UHFFFAOYSA-N n-benzyl-2-fluoro-4-nitroaniline Chemical compound FC1=CC([N+](=O)[O-])=CC=C1NCC1=CC=CC=C1 NTPGVWDPQFFUSU-UHFFFAOYSA-N 0.000 description 1
- 208000004235 neutropenia Diseases 0.000 description 1
- 210000000440 neutrophil Anatomy 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910000510 noble metal Inorganic materials 0.000 description 1
- 208000015380 nutritional deficiency disease Diseases 0.000 description 1
- 230000033660 oral incubation Effects 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 239000012285 osmium tetroxide Substances 0.000 description 1
- 229910000489 osmium tetroxide Inorganic materials 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000001814 pectin Substances 0.000 description 1
- 235000010987 pectin Nutrition 0.000 description 1
- 229920001277 pectin Polymers 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- 238000009521 phase II clinical trial Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- XKJCHHZQLQNZHY-UHFFFAOYSA-N phthalimide Chemical compound C1=CC=C2C(=O)NC(=O)C2=C1 XKJCHHZQLQNZHY-UHFFFAOYSA-N 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- TZLVRPLSVNESQC-UHFFFAOYSA-N potassium azide Chemical compound [K+].[N-]=[N+]=[N-] TZLVRPLSVNESQC-UHFFFAOYSA-N 0.000 description 1
- HDMGAZBPFLDBCX-UHFFFAOYSA-M potassium;sulfooxy sulfate Chemical compound [K+].OS(=O)(=O)OOS([O-])(=O)=O HDMGAZBPFLDBCX-UHFFFAOYSA-M 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- ALDITMKAAPLVJK-UHFFFAOYSA-N prop-1-ene;hydrate Chemical group O.CC=C ALDITMKAAPLVJK-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N propylene glycol Substances CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 1
- 125000006239 protecting group Chemical group 0.000 description 1
- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910001927 ruthenium tetroxide Inorganic materials 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 238000010956 selective crystallization Methods 0.000 description 1
- 239000012056 semi-solid material Substances 0.000 description 1
- 210000002966 serum Anatomy 0.000 description 1
- 238000000526 short-path distillation Methods 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001509 sodium citrate Substances 0.000 description 1
- NLJMYIDDQXHKNR-UHFFFAOYSA-K sodium citrate Chemical compound O.O.[Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O NLJMYIDDQXHKNR-UHFFFAOYSA-K 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- 239000007909 solid dosage form Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000010561 standard procedure Methods 0.000 description 1
- 239000001119 stannous chloride Substances 0.000 description 1
- 235000011150 stannous chloride Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 229940031000 streptococcus pneumoniae Drugs 0.000 description 1
- 238000007920 subcutaneous administration Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 229940086735 succinate Drugs 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000829 suppository Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 229940042055 systemic antimycotics triazole derivative Drugs 0.000 description 1
- 229940037128 systemic glucocorticoids Drugs 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 125000004187 tetrahydropyran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 206010043554 thrombocytopenia Diseases 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- LBLYYCQCTBFVLH-UHFFFAOYSA-M toluenesulfonate group Chemical group C=1(C(=CC=CC1)S(=O)(=O)[O-])C LBLYYCQCTBFVLH-UHFFFAOYSA-M 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000041 toxicology testing Toxicity 0.000 description 1
- 238000002627 tracheal intubation Methods 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- MYPYJXKWCTUITO-LYRMYLQWSA-N vancomycin Chemical compound O([C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C2C=C3C=C1OC1=CC=C(C=C1Cl)[C@@H](O)[C@H](C(N[C@@H](CC(N)=O)C(=O)N[C@H]3C(=O)N[C@H]1C(=O)N[C@H](C(N[C@@H](C3=CC(O)=CC(O)=C3C=3C(O)=CC=C1C=3)C(O)=O)=O)[C@H](O)C1=CC=C(C(=C1)Cl)O2)=O)NC(=O)[C@@H](CC(C)C)NC)[C@H]1C[C@](C)(N)[C@H](O)[C@H](C)O1 MYPYJXKWCTUITO-LYRMYLQWSA-N 0.000 description 1
- 229960003165 vancomycin Drugs 0.000 description 1
- MYPYJXKWCTUITO-UHFFFAOYSA-N vancomycin Natural products O1C(C(=C2)Cl)=CC=C2C(O)C(C(NC(C2=CC(O)=CC(O)=C2C=2C(O)=CC=C3C=2)C(O)=O)=O)NC(=O)C3NC(=O)C2NC(=O)C(CC(N)=O)NC(=O)C(NC(=O)C(CC(C)C)NC)C(O)C(C=C3Cl)=CC=C3OC3=CC2=CC1=C3OC1OC(CO)C(O)C(O)C1OC1CC(C)(N)C(O)C(C)O1 MYPYJXKWCTUITO-UHFFFAOYSA-N 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 235000019786 weight gain Nutrition 0.000 description 1
- 208000016261 weight loss Diseases 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Animal Behavior & Ethology (AREA)
- Pharmacology & Pharmacy (AREA)
- General Chemical & Material Sciences (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Epidemiology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US38427895A | 1995-02-03 | 1995-02-03 | |
PCT/US1996/000718 WO1996023788A1 (en) | 1995-02-03 | 1996-01-29 | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
Publications (3)
Publication Number | Publication Date |
---|---|
NO973550D0 NO973550D0 (no) | 1997-08-01 |
NO973550L NO973550L (no) | 1997-10-03 |
NO309526B1 true NO309526B1 (no) | 2001-02-12 |
Family
ID=23516681
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
NO973550A NO309526B1 (no) | 1995-02-03 | 1997-08-01 | Hetero-aromatiske ring-substituerte fenyloksazolidinon- antimikrobielle midler og anvendelse av disse for fremstilling av et medikament |
Country Status (20)
Country | Link |
---|---|
US (1) | US5910504A (fi) |
EP (1) | EP0807112B1 (fi) |
JP (1) | JPH10513446A (fi) |
KR (1) | KR100441334B1 (fi) |
CN (1) | CN1075073C (fi) |
AT (1) | ATE205205T1 (fi) |
BR (1) | BR9607017A (fi) |
CA (1) | CA2208603A1 (fi) |
CZ (1) | CZ231497A3 (fi) |
DE (1) | DE69615002T2 (fi) |
DK (1) | DK0807112T3 (fi) |
ES (1) | ES2163004T3 (fi) |
FI (1) | FI973217A0 (fi) |
HK (1) | HK1008898A1 (fi) |
NO (1) | NO309526B1 (fi) |
NZ (1) | NZ302844A (fi) |
PL (1) | PL185872B1 (fi) |
PT (1) | PT807112E (fi) |
RU (1) | RU2154645C2 (fi) |
WO (1) | WO1996023788A1 (fi) |
Families Citing this family (69)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1075073C (zh) * | 1995-02-03 | 2001-11-21 | 法玛西雅厄普约翰美国公司 | 杂芳环取代的苯基噁唑烷酮抗菌剂 |
US6124334A (en) * | 1995-02-03 | 2000-09-26 | Pharmacia & Upjohn Company | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials |
JPH11512429A (ja) * | 1995-09-15 | 1999-10-26 | ファルマシア・アンド・アップジョン・カンパニー | アミノアリールオキサゾリジノン n−オキシド |
GB9601666D0 (en) * | 1996-01-27 | 1996-03-27 | Zeneca Ltd | Chemical compounds |
GB9702213D0 (en) * | 1996-02-24 | 1997-03-26 | Zeneca Ltd | Chemical compounds |
GB9604301D0 (en) * | 1996-02-29 | 1996-05-01 | Zeneca Ltd | Chemical compounds |
GB9609919D0 (en) * | 1996-05-11 | 1996-07-17 | Zeneca Ltd | Chemical compounds |
DE19709443C1 (de) * | 1997-03-07 | 1998-10-08 | Clariant Gmbh | Verfahren zur Herstellung von N-Carboxyalkyl-3-fluor-4-dialkylaminoanilinen und N-Carboxymethyl-3-fluor-4-morpholinoanilin und N-Carboxyisobutyl-3-fluor-4-morpholinoanilin |
DE19750968A1 (de) * | 1997-03-07 | 1998-09-10 | Clariant Gmbh | Verfahren zur Herstellung von N-Carboxyalkyl-3-fluor-4-dialkylaminoanilinen |
CA2294293A1 (en) * | 1997-07-11 | 1999-01-21 | Pharmacia & Upjohn Company | Thiadiazolyl and oxadiazolyl phenyl oxazolidinone antibacterial agents |
GB9717804D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
GB9717807D0 (en) | 1997-08-22 | 1997-10-29 | Zeneca Ltd | Chemical compounds |
GB9725244D0 (en) * | 1997-11-29 | 1998-01-28 | Zeneca Ltd | Chemical compounds |
ATE222894T1 (de) * | 1998-02-13 | 2002-09-15 | Upjohn Co | Substituierte aminophenylisoxazolinderivate verwendbar als antimikrobielle agenzien |
AU3180999A (en) * | 1998-02-25 | 1999-09-15 | Pharmacia & Upjohn Company | Substituted aminomethyl isoxazoline derivatives useful as antimicrobials |
KR20010052615A (ko) | 1998-06-05 | 2001-06-25 | 다비드 에 질레스 | 옥사졸리디논 유도체, 이것의 제조 방법 및 이것을함유하는 약학 조성물 |
WO2000045177A1 (en) | 1999-01-27 | 2000-08-03 | Pharmacia & Upjohn Company | Assays for modulators of elongation factor p activity |
US6608081B2 (en) | 1999-08-12 | 2003-08-19 | Ortho-Mcneil Pharmaceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
US6297242B1 (en) * | 1999-08-12 | 2001-10-02 | Ortho-Mcneil Pharmaceutical, Inc. | N-substituted amidine and guanidine oxazolidinone antibacterials and methods of use thereof |
US6413981B1 (en) * | 1999-08-12 | 2002-07-02 | Ortho-Mcneil Pharamceutical, Inc. | Bicyclic heterocyclic substituted phenyl oxazolidinone antibacterials, and related compositions and methods |
GB9928568D0 (en) | 1999-12-03 | 2000-02-02 | Zeneca Ltd | Chemical compounds |
US6518285B2 (en) | 1999-12-21 | 2003-02-11 | Ortho Mcneil Pharmaceutical, Inc. | Piperidinyloxy and pyrrolidinyloxy oxazolidinone antibacterials |
DE19962924A1 (de) * | 1999-12-24 | 2001-07-05 | Bayer Ag | Substituierte Oxazolidinone und ihre Verwendung |
GB0009803D0 (en) * | 2000-04-25 | 2000-06-07 | Astrazeneca Ab | Chemical compounds |
PE20020300A1 (es) * | 2000-08-22 | 2002-05-10 | Pharmacia Corp | Composicion de solucion de un farmaco antibiotico a base de oxazolidinona con mejoramiento de la carga de farmaco |
US6861433B2 (en) * | 2000-12-15 | 2005-03-01 | Pharmacia & Upjohn Company | Oxazolidinone photoaffinity probes |
WO2002064574A2 (en) * | 2001-02-07 | 2002-08-22 | Ortho-Mcneil Pharmaceutical, Inc. | Pyridoarylphenyl oxazolidinone antibacterials, and related compositions and methods |
DE10129725A1 (de) * | 2001-06-20 | 2003-01-02 | Bayer Ag | Kombinationstherapie substituierter Oxazolidinone |
US7141588B2 (en) | 2002-02-25 | 2006-11-28 | Pfizer, Inc. | N-aryl-2-oxazolidinone-5-carboxamides and their derivatives |
AR038536A1 (es) | 2002-02-25 | 2005-01-19 | Upjohn Co | N-aril-2-oxazolidinona-5- carboxamidas y sus derivados |
WO2003106454A1 (en) * | 2002-06-12 | 2003-12-24 | Orchid Chemicals & Pharmaceuticals Ltd | 1h-isoquinoline-oxazolidinone derivaties and their use as antibacterial agents |
CA2491287A1 (en) | 2002-08-12 | 2004-02-19 | Pharmacia & Upjohn Company | N-aryl-2-oxazolidinones and their derivatives |
AU2002339721A1 (en) * | 2002-09-20 | 2004-04-08 | Lupin Limited | Oxazolidinone derivatives, process for their preperation and their use as antimycobacterial agents |
BR0316483A (pt) | 2002-11-21 | 2005-10-11 | Upjohn Co | Derivados de n-(4-(piperazin-1-il)-fenil-2-oxazolidinona-5-carboxami da e compostos relacionados como agentes antibacterianos |
DE10300111A1 (de) * | 2003-01-07 | 2004-07-15 | Bayer Healthcare Ag | Verfahren zur Herstellung von 5-Chlor-N-({(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophencarboxamid |
US7304050B2 (en) | 2003-09-16 | 2007-12-04 | Pfizer Inc. | Antibacterial agents |
DE10355461A1 (de) | 2003-11-27 | 2005-06-23 | Bayer Healthcare Ag | Verfahren zur Herstellung einer festen, oral applizierbaren pharmazeutischen Zusammensetzung |
DE102004062475A1 (de) * | 2004-12-24 | 2006-07-06 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit modifizierter Freisetzung |
EP1685841A1 (en) * | 2005-01-31 | 2006-08-02 | Bayer Health Care Aktiengesellschaft | Prevention and treatment of thromboembolic disorders |
US20060258691A1 (en) * | 2005-05-13 | 2006-11-16 | Joseph Barbosa | Methods and compositions for improving cognition |
AU2006283511A1 (en) * | 2005-08-24 | 2007-03-01 | Lexicon Pharmaceuticals, Inc. | Pyrrolopyridine, pyrrolopyrimidine and pyrazolopyridine compounds, compositions comprising them, and methods of their use |
DE102005045518A1 (de) * | 2005-09-23 | 2007-03-29 | Bayer Healthcare Ag | 2-Aminoethoxyessigsäure-Derivate und ihre Verwendung |
DE102005047561A1 (de) | 2005-10-04 | 2007-04-05 | Bayer Healthcare Ag | Feste, oral applizierbare pharmazeutische Darreichungsformen mit schneller Wirkstofffreisetzung |
CA2624310C (en) | 2005-10-04 | 2014-01-07 | Bayer Healthcare Ag | Polymorphic form of 5-chloro-n-({5s)-2-oxo-3-[4-(3-oxo-4-morpholinyl)-phenyl]-1,3-oxazolidin-5-yl}-methyl)-2-thiophenecarboxamide |
DE102005047558A1 (de) * | 2005-10-04 | 2008-02-07 | Bayer Healthcare Ag | Kombinationstherapie substituierter Oxazolidinone zur Prophylaxe und Behandlung von cerebralen Durchblutungsstörungen |
US7547421B2 (en) * | 2006-10-18 | 2009-06-16 | Ecolab Inc. | Apparatus and method for making a peroxycarboxylic acid |
DE102006051625A1 (de) * | 2006-11-02 | 2008-05-08 | Bayer Materialscience Ag | Kombinationstherapie substituierter Oxazolidinone |
WO2008143649A2 (en) * | 2006-12-04 | 2008-11-27 | Dr. Reddy's Laboratories Limited | Novel oxazolidinone compounds as antiinfective agents |
KR100872059B1 (ko) | 2007-02-21 | 2008-12-05 | 주식회사 레고켐 바이오사이언스 | 아미독심 또는 하이드록사마이드 기를 가지는 신규한옥사졸리디논 유도체 및 이를 함유하는 의약 조성물 |
EP2072514A1 (en) * | 2007-12-17 | 2009-06-24 | Ferrer Internacional, S.A. | 1(2)H-tetrazol-5-yl-phenyl-oxazolidinones as antibacterial agents |
CN102827155B (zh) * | 2011-06-17 | 2015-03-25 | 四川大学 | 噁唑烷酮类化合物及其在制备抗生素药物中的用途 |
EP2602248A1 (en) | 2011-12-05 | 2013-06-12 | University Of Leicester | Novel pyrrole compounds |
CN104364240B (zh) * | 2012-06-08 | 2017-02-22 | 四川贝力克生物技术有限责任公司 | 一种用于预防或治疗分支杆菌疾病的药物 |
CN104873510B (zh) * | 2014-02-28 | 2019-03-19 | 四川好医生药业集团有限公司 | 噁唑烷酮类化合物抗生物膜用途 |
CN103965183B (zh) * | 2014-03-17 | 2017-05-03 | 上海应用技术学院 | 一种含氟噁唑烷酮类化合物及其制备方法和应用 |
CN105272976B (zh) * | 2014-07-22 | 2018-11-20 | 四川好医生药业集团有限公司 | 一种噁唑烷酮类化合物 |
CN105399737B (zh) * | 2014-09-10 | 2018-09-21 | 四川好医生药业集团有限公司 | 噁唑烷酮类化合物及其用途 |
US9573936B2 (en) | 2015-05-20 | 2017-02-21 | Amgen Inc. | Triazole agonists of the APJ receptor |
US9988369B2 (en) | 2016-05-03 | 2018-06-05 | Amgen Inc. | Heterocyclic triazole compounds as agonists of the APJ receptor |
EP3541805B1 (en) | 2016-11-16 | 2020-10-14 | Amgen Inc. | Heteroaryl-substituted triazoles as apj receptor agonists |
WO2018093580A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole pyridyl compounds as agonists of the apj receptor |
EP3541804A1 (en) | 2016-11-16 | 2019-09-25 | Amgen Inc. | Cycloalkyl substituted triazole compounds as agonists of the apj receptor |
WO2018093579A1 (en) | 2016-11-16 | 2018-05-24 | Amgen Inc. | Triazole phenyl compounds as agonists of the apj receptor |
MA46824A (fr) | 2016-11-16 | 2019-09-25 | Amgen Inc | Composés de triazole substitués par alkyle en tant qu'agonistes du récepteur apj |
WO2018097944A1 (en) | 2016-11-16 | 2018-05-31 | Amgen Inc. | Triazole furan compounds as agonists of the apj receptor |
CN106831615B (zh) * | 2017-02-15 | 2019-02-15 | 南京农业大学 | 一类1,2,3-三唑-5-酰胺类化合物作为农用杀菌剂的应用 |
EP3704122B1 (en) | 2017-11-03 | 2021-09-01 | Amgen Inc. | Fused triazole agonists of the apj receptor |
WO2019213006A1 (en) | 2018-05-01 | 2019-11-07 | Amgen Inc. | Substituted pyrimidinones as agonists of the apj receptor |
CN113372276B (zh) * | 2021-05-25 | 2022-04-22 | 三峡大学 | 吲唑类衍生物及其应用 |
Family Cites Families (16)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4801600A (en) * | 1987-10-09 | 1989-01-31 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
US4921869A (en) * | 1987-10-09 | 1990-05-01 | E. I. Du Pont De Nemours And Company | Aminomethyl oxooxazolidinyl cycloalkylbenzene derivatives useful as antibacterial agents |
CA1320730C (en) * | 1987-10-16 | 1993-07-27 | The Du Pont Merck Pharmaceutical Company | Aminomethyl oxooxazolidinyl aroylbenzene derivatives useful as antibacterial agents |
ATE95176T1 (de) * | 1987-10-21 | 1993-10-15 | Du Pont Merck Pharma | Aminomethyl-oxo-oxazolidinyl-ethenylbenzenderivate, nuetzlich als antibakterielles mittel. |
US4948801A (en) * | 1988-07-29 | 1990-08-14 | E. I. Du Pont De Nemours And Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
US5254577A (en) * | 1988-07-29 | 1993-10-19 | The Du Pont Merck Pharmaceutical Company | Aminomethyloxooxazolidinyl arylbenzene derivatives useful as antibacterial agents |
WO1990002744A1 (en) * | 1988-09-15 | 1990-03-22 | The Upjohn Company | In position 3 substituted-5-beta-amidomethyl-oxazolidin-2-ones |
JP3176626B2 (ja) * | 1991-11-01 | 2001-06-18 | ファルマシア・アンド・アップジョン・カンパニー | 抗菌剤として有用な置換アリール−およびヘテロアリールフェニルオキサゾリジノン類 |
SK283420B6 (sk) * | 1992-05-08 | 2003-07-01 | Pharmacia & Upjohn Company | Antimikrobiálne oxazolidinóny obsahujúce substituované diazínové skupiny |
MY115155A (en) * | 1993-09-09 | 2003-04-30 | Upjohn Co | Substituted oxazine and thiazine oxazolidinone antimicrobials. |
DE4332384A1 (de) * | 1993-09-23 | 1995-03-30 | Merck Patent Gmbh | Adhäsionsrezeptor-Antagonisten III |
US5668286A (en) * | 1994-03-15 | 1997-09-16 | Pharmacia & Upjohn Company | Oxazolidinone derivatives and pharmaceutical compositions containing them |
DE4425609A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | Benzofuranyl- und Benzothienyloxazolidinone |
DE4425613A1 (de) * | 1994-07-20 | 1996-01-25 | Bayer Ag | 5-gliedrige Heteroaryl-oxazolidinone |
CN1075073C (zh) * | 1995-02-03 | 2001-11-21 | 法玛西雅厄普约翰美国公司 | 杂芳环取代的苯基噁唑烷酮抗菌剂 |
GB9604301D0 (en) * | 1996-02-29 | 1996-05-01 | Zeneca Ltd | Chemical compounds |
-
1996
- 1996-01-29 CN CN96191740A patent/CN1075073C/zh not_active Expired - Fee Related
- 1996-01-29 BR BR9607017A patent/BR9607017A/pt not_active Application Discontinuation
- 1996-01-29 CA CA002208603A patent/CA2208603A1/en not_active Abandoned
- 1996-01-29 EP EP96905168A patent/EP0807112B1/en not_active Expired - Lifetime
- 1996-01-29 US US08/875,800 patent/US5910504A/en not_active Expired - Fee Related
- 1996-01-29 NZ NZ302844A patent/NZ302844A/xx unknown
- 1996-01-29 JP JP8523572A patent/JPH10513446A/ja not_active Withdrawn
- 1996-01-29 ES ES96905168T patent/ES2163004T3/es not_active Expired - Lifetime
- 1996-01-29 DK DK96905168T patent/DK0807112T3/da active
- 1996-01-29 KR KR1019970705305A patent/KR100441334B1/ko not_active IP Right Cessation
- 1996-01-29 PT PT96905168T patent/PT807112E/pt unknown
- 1996-01-29 AT AT96905168T patent/ATE205205T1/de not_active IP Right Cessation
- 1996-01-29 CZ CZ972314A patent/CZ231497A3/cs unknown
- 1996-01-29 PL PL96321663A patent/PL185872B1/pl not_active IP Right Cessation
- 1996-01-29 DE DE69615002T patent/DE69615002T2/de not_active Expired - Fee Related
- 1996-01-29 WO PCT/US1996/000718 patent/WO1996023788A1/en not_active Application Discontinuation
- 1996-01-29 RU RU97114833/04A patent/RU2154645C2/ru not_active IP Right Cessation
-
1997
- 1997-08-01 NO NO973550A patent/NO309526B1/no not_active IP Right Cessation
- 1997-08-04 FI FI973217A patent/FI973217A0/fi unknown
-
1998
- 1998-08-04 HK HK98109662A patent/HK1008898A1/xx not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NO973550L (no) | 1997-10-03 |
DE69615002T2 (de) | 2002-06-13 |
DE69615002D1 (de) | 2001-10-11 |
WO1996023788A1 (en) | 1996-08-08 |
NO973550D0 (no) | 1997-08-01 |
FI973217A (fi) | 1997-08-04 |
BR9607017A (pt) | 1997-10-28 |
NZ302844A (en) | 1999-06-29 |
RU2154645C2 (ru) | 2000-08-20 |
PL185872B1 (pl) | 2003-08-29 |
AU4899896A (en) | 1996-08-21 |
AU703465B2 (en) | 1999-03-25 |
EP0807112B1 (en) | 2001-09-05 |
ATE205205T1 (de) | 2001-09-15 |
US5910504A (en) | 1999-06-08 |
EP0807112A1 (en) | 1997-11-19 |
KR100441334B1 (ko) | 2004-10-20 |
CN1172484A (zh) | 1998-02-04 |
PL321663A1 (en) | 1997-12-22 |
CN1075073C (zh) | 2001-11-21 |
JPH10513446A (ja) | 1998-12-22 |
HK1008898A1 (en) | 1999-07-23 |
DK0807112T3 (da) | 2001-12-17 |
ES2163004T3 (es) | 2002-01-16 |
PT807112E (pt) | 2002-02-28 |
KR19980701908A (ko) | 1998-06-25 |
CA2208603A1 (en) | 1996-08-08 |
FI973217A0 (fi) | 1997-08-04 |
CZ231497A3 (cs) | 1998-08-12 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
NO309526B1 (no) | Hetero-aromatiske ring-substituerte fenyloksazolidinon- antimikrobielle midler og anvendelse av disse for fremstilling av et medikament | |
RU2128660C1 (ru) | Бициклические оксазин- или тиазин-оксазолидиноны или их фармацевтически приемлемые соли и способы лечения микробных инфекций | |
US6090820A (en) | Spirocyclic and bicyclic diazinyl and carbazinyl oxazolidinones | |
EP0750618B1 (en) | Oxazolidinone derivatives and pharmaceutical compositions containing them | |
US5668286A (en) | Oxazolidinone derivatives and pharmaceutical compositions containing them | |
US6124334A (en) | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials | |
US6069141A (en) | Substituted aminophenyl isoxazoline derivatives useful as antimicrobials | |
JPH09502436A (ja) | 置換オキサジンおよびチアジンオキサゾリジノン抗微生物剤 | |
ZA200505225B (en) | Antibacterial indolone oxazolidinones, intermediates for their preparation and pharmaceutical compositions containing them | |
RU2215740C2 (ru) | Оксазолидиноновые производные и фармацевтические композиции на их основе | |
WO2007093904A1 (en) | Benzoxazinone and benzoxazepinone oxazolidinones as antibacterial agents | |
US5929083A (en) | Oxazolidinone derivatives and a method for the preparation thereof and an antibacterial composition containing the same | |
AU703465C (en) | Hetero-aromatic ring substituted phenyloxazolidinone antimicrobials | |
KR100463111B1 (ko) | 신규한옥사졸리디논유도체및제조방법및그를함유하는항균제조성물 | |
CA2201736A1 (en) | Bicyclic oxazine and thiazine oxazolidinone antibacterials | |
CZ20001687A3 (cs) | Deriváty oxazolidinonu a farmaceutické kompozice |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
MM1K | Lapsed by not paying the annual fees |